Conversion Of 1-decene Research Articles

Selective catalytic conversion of model olefin and diolefin compounds of waste plastic pyrolysis oil: Insights for light olefin production and coke minimization

The primary challenges in ex-situ catalytic pyrolysis of plastic waste to produce light olefins lie in the selective conversion of larger olefins and diolefins downstream of the pyrolyzer. Hence, the catalytic cracking mechanism of plastic pyrolysis oil was explored using an α-olefin (1-decene) and a diolefin (1,9-decadiene) model compounds over an HZSM-5 zeolite-based catalyst in a fixed-bed reactor. Key objectives were to elucidate the reaction pathways for light olefin production, aromatization, and coke formation in catalytic cracking of larger olefins and diolefins. The investigation explored the impact of HZSM-5 steam treatment severity, contact time (∼58–226 ms), and reaction temperature (250–450 °C) on product yields. The severity of steam treatment was found to increase the 1-decene isomerization rate while decreasing the cracking rate and conversion of 1-decene to C3-4 light olefins. In the catalytic cracking of 1-decene, major product types included olefins (linear and nonlinear) and a few naphthenes, while in the case of 1,9-decadiene catalytic cracking, non-linear olefins were absent, with abundant naphthenes followed by lighter diolefins and C3-5 linear olefins. Temperature and contact time variations revealed that the catalytic cracking of 1-decene initiated with double bond rearrangement isomerization, progressing to skeletal isomerization, and intensified cracking reactions producing light C3-4 olefins. Conversely, in the catalytic cracking of 1,9-decadiene, cyclization was the primary reaction pathway, followed by β-scission, resulting in lighter conjugated dienes and light linear olefins. Thermal gravimetric analysis (TGA) of spent catalysts confirmed a higher coke amount generated during 1,9-decadiene cracking compared to 1-decene cracking, indicating that diene compounds serve as precursors for significant coke formation in plastic pyrolysis oil. These insights provide valuable understanding for catalytic upgrading of pyrolysis oil from polyolefin pyrolysis.

Titanium Salalen Catalyzed Enantioselective Benzylic Hydroxylation.

The titanium complex of the cis-1,2-diaminocyclohexane (cis-DACH) derived Berkessel-salalen ligand is a highly efficient and enantioselective catalyst for the asymmetric epoxidation of terminal olefins with hydrogen peroxide ("Berkessel-Katsuki catalyst"). We herein report that this epoxidation catalyst also effects the highly enantioselective hydroxylation of benzylic C-H bonds with hydrogen peroxide. Mechanism-based ligand optimization identified a novel nitro-salalen Ti-catalyst of the highest efficiency ever reported for asymmetric catalytic benzylic hydroxylation, with enantioselectivities of up to 98 % ee, while overoxidation to ketone is marginal. The novel nitro-salalen Ti-catalyst also shows enhanced epoxidation efficiency, as evidenced by e.g. the conversion of 1-decene to its epoxide in 90 % yield with 94 % ee, at a catalyst loading of 0.1 mol-% only.

Kinetic modeling of 1-decene oligomerization to synthetic fuels and base oil over tungstated-zirconia catalyst

The liquid phase oligomerization reaction of 1-decene to produce dimers and trimers was performed in a semi-batch autoclave reactor over a tungstated-zirconia catalyst at different reaction temperatures. While dimers can be used as a synthetic transportation fuel, trimers and higher compounds can be used as a base oil which can be blended with additives to make synthetic base oil. The conversion of 1-decene increased from 9 to 70% as the reaction temperature was increased from 423 to 483 K. At 483 K, product compositions after 11 h consisted of 50% dimers and 23% trimers. Apparent activation energies for dimerization and trimerization were found to be 21.0 ± 0.5 and 33.0 ± 0.6 kJ/mol, respectively. Kinetic interpretation has been made by studying the kinetic and equilibrium constants. The results of the oligomerization of 1-decene suggest that two active sites are responsible for dimerization. Trimerization proceeds through a combination of dimer with another monomer involving three active sites. According to the mathematical equation, an increase in active sites required for both reactions at higher temperature is necessary to compensate for catalyst deactivation.

Oligomerization of 1-decene over sulfated alumina catalysts for the production of synthetic fuels and lubricants: modelling and verification

The three-factor Box-Behnken design and the response surface methodology (RSM) were used to optimize the production of C20 (transportation fuel) and C30 + (lubricant oil) hydrocarbons obtained from 15 different oligomerization reactions of 1-decene over sulfated alumina catalysts in batch operation mode. The physiochemical properties of the sulfated alumina catalysts were characterized by N2 sorption, XRD and NH3-TPD. The formulated quadratic models as a function of three independent variables of reaction temperature (448–473 K), sulfuric acid concentration (2.5–4.5 M) and catalyst amount (5–15 wt%) were verified by the experimental results (1-decene conversion and product composition) with a coefficient of determination higher than 0.97 for all dependent variables (conversion, amount of C20 and C30 +). The optimal amount of C20 (65.4 wt%) was achieved at 473 K, using 3.5 M sulfated alumina and 8.8 wt% of catalyst. Similarly, the optimization of C30 + (47.7 wt%) was revealed at 473 K, using 3.5 M sulfated alumina and 15 wt% of catalyst. It was concluded that oligomerization over sulfated alumina was successfully optimized using Box-Behnken design.

Highly selective olefin hydrogenation: Refinery oil upgrading over bifunctional PdOx/H-ZSM-5 catalyst

A novel strategy is reported in this study to design a novel bifunctional PdOx/H-ZSM-5 catalyst for selective hydrogenation of olefin. PdOx species (basic oxides) anchored on the strong acidic sites (Brönsted acid sites) of zeolite support could not only generate new acidic sites with moderate acidic strength but also exhibit good capability for H2 activation and dissociation. The conversion of 1-decene is 100% and total selectivity of methyl-nonane is 98.4±0.4% at 350°C. Our research might provide a valuable approach to design a highly efficient bifunctional catalyst for olefin upgrading.

The Application of Silica-Supported Preyssler HPA as a Heterogeneous and Green Catalyst for the Alkylation of Benzene

Liquid-phase alkylation of benzene with 1-decene for the production of linear alkylbenzene (LAB) was investigated with silica-supported Preyssler heteropoly acid as the catalyst. Catalyst loading, Bz/C10 molar ratio, and catalyst weight percentage were investigated. Catalyst with 30% loading, Bz/C10 molar ratio of 17, and catalyst weight percentage of 2.6 showed 1-decene conversion of 100% and 2-phenyl decane selectivity of 27.2% at 80°C and 2-hr reaction.

Preparation of an active and regenerable catalyst for liquid-phase alkylation of toluene with 1-decene

Zeolite Y was tested as an alternative solid acid catalyst for the production of linear alkyl aromatics with the emphasis on its activity and stability towards regeneration. Liquid-phase alkylation of toluene with 1-decene at 100°C was used as the model reaction. Deactivated catalyst samples were regenerated by the temperature programmed calcination (TPC) in air flow at 550°C. The activity of the unmodified HY zeolite during alkylation was significant but decreased to a minimum after regeneration, as a result of a partial structure collapse during regeneration using TPC. To avoid the structure collapse hydrothermal stabilization of zeolite Y at 560, 670 and 780°C was performed. Subsequent chemical dealumination using 0.5M HCl or ion-exchange with the 2M NH4NO3 solution, in order to improve the catalyst activity, were carried out. All the samples were then tested in alkylation. The main monitored parameters were the conversion of 1-decene, selectivity to 2-phenyldecane isomer and the amount of side-products. The sample stabilized at 560°C and ion-exchanged subsequently showed the highest activity with the lowest amount of by-products. This sample was also regenerated and reused four times in the cycle alkylation–regeneration with no loss of structure or activity. In fact there was a slight activity increase of this sample after regeneration.

Comparison of RSM and ANN for the investigation of linear alkylbenzene synthesis over H14[NaP5W30O110]/SiO2 catalyst

Design of experiments (DOE) and artificial neural networks (ANNs) were successfully applied for studying the operating parameters of benzene alkylation with 1-decene over H14[NaP5W30O110]/SiO2 catalyst. In this reaction catalyst loading, catalyst weight percent and benzene to 1-decene molar ratio (Bz/C10) were chosen as independent variables in experimental design. Prediction of 1-decene conversion and 2-phenyldecane selectivity was performed applying response surface method (RSM) and ANN models. Final selected multi-layer (3-6-2-2) ANN model resulted a coefficient of determination (R2) of 0.95 for 1-decene conversion and 0.99 for 2-phenyldecane selectivity, while the R2 of RSM was 0.93 and 0.92 for these two parameters.

Surface properties of pillared acid-activated bentonite as catalyst for selective production of linear alkylbenzene

Acid-activated and pillared montmorillonite were prepared as novel catalysts for alkylation of benzene with 1-decene for production of linear alkylbenzene. The catalysts were characterized by X-ray diffraction, FT-IR spectroscopy, N2 adsorption isotherms, temperature programmed desorption of NH3, scanning electron microscopy and elemental and thermal analysis techniques. It was found that acid-activation of clays prior to pillaring increased the porosity, total specific surface area, total pore volume and surface acidity of the catalysts. Optimization of the reaction conditions was performed by varying catalyst concentration (0.25–1.75wt%), reactants ratio (benzene to 1-decene of 8.75, 12 and 15) and temperature (115–145°C) in a batch slurry reactor. Under optimized conditions more than 98% conversion of 1-decene, and complete selectivity for monoalkylbenzenes were achieved.

A novel catalyst for alkylation of benzene

Abstract In this research, acid-activated and pillared montmorillonite were prepared as catalysts for alkylation of benzene with 1-decene for production of linear alkyl bebzene (LAB). The catalysts were characterized by X-ray diffraction (XRD), FT-IR spectroscopy, scanning electron microscopy (SEM), N2 adsorption-desorption isotherms, temperature programmed desorption (TPD) of NH3 and elemental and thermal analysis techniques. The reaction conditions were optimized by varying catalyst concentration, reactants ratio and temperature in a batch-slurry reactor. It was found that acid-activation increased the porosity and surface acidity of the catalysts. Pillaring of the sample improved the surface area, micro-mesoporosity and acidity. Under optimized conditions more than 98% conversion of 1-decene was observed. All products were LABs and no major side reaction was observed.

Alkylation of Benzene with 1-Decene Using Silica Supported Preyssler Heteropoly Acid: Statistical Design with Response Surface Methodology

The response surface method (RSM) was applied to study the liquid phase alkylation of benzene with 1-decene catalyzed by means of silica supported Preyssler heteropoly acid. A three step experimental design was developed based on the central composite design (CCD). Catalyst loading, catalyst mass percent, and benzene to 1-decene molar ratio were used to optimize 1-decene conversion and linear alkylbenzene (LAB) yield. The results indicated that the quadratic model was significant for these two responses. The experimental results revealed that all variables had positive effect on 1-decene conversion. While increasing the catalyst loading tends to decrease LAB yield. Benzene to 1-decene molar ratio was found to be the most important factor that influenced LAB yield with a positive effect. Design expert software suggested several optimized solutions, among them the best choice was to use 31% catalyst loading, benzene to 1-decene molar ratio of 13, and catalyst percent of 3.6 wt% for obtaining 100% conversion and 88% LAB production yield.

Investigation of Silica-Supported Preyssler Nanoparticles as Nanocatalysts in Alkylation of Benzene With 1-Decene Using Artificial Intelligence Approach

Silica-supported Preyssler nanoparticles were synthesized and tested in alkylation of benzene with 1-decene. Adaptive network based fuzzy inference system (ANFIS) was successfully applied for studying the operating parameters of this catalytic reaction. The reaction was carried out at a constant temperature of 80 °C for 2 h, while catalyst loading, catalyst weight percent, and benzene to 1-decene molar ratio (Bz/C10) were chosen as independent variables. Prediction of 1-decene conversion and linear alkylbenzene (LAB) production yield were performed by applying ANFIS method. The predictive ability and accuracy of ANFIS model were examined using unseen experimental data set and R2 was obtained to be 0.994 and 0.995 for 1-decene conversion and LAB production yield, respectively. Experimental results revealed that catalyst loading, Bz/C10 molar ratio, and catalyst weight percent have positive effect on 1-decene conversion, while increase in catalyst loading tends to decrease LAB production yield.

Reaction Mechanism and in Situ ATR Spectroscopic Studies of the 1-Decene Ozonolysis in Micro- and Semibatch Reactors

The ozonolysis of 1-decene (1) was performed in a falling film microreactor and in a semibatch reactor using different solvents (CH2Cl2, CH3OH, or a mixture of both). The main products of ozonolysis were 3-octyl-1,2,4-trioxolane (7) in CH2Cl2 and 1-hydroperoxy-1-methoxynonane (8) in CH3OH or in a CH2Cl2/CH3OH mixture. In both cases the selectivities were higher than 70% and almost independent of 1-decene conversion and reaction temperature. The ozonolysis proceeds mainly via the cleavage of the primary ozonide into the long-chain carbonyl oxide (6) and formaldehyde (4). Besides off-line analysis in situ ATR-FTIR spectroscopic measurements using a diamond ATR probe were applied to follow the reaction progress. Integral intensities of characteristic IR bands correlate well with quantitative results obtained from gas chromatography/high-performance liquid chromatography analysis. Thus, in situ ATR proved to be a suitable method for fast and real-time monitoring of liquid-phase reactions even in the presence of unstable or explosive intermediates like ozonides and/or hydroperoxides.

Study on Preparation Process of Lubrication from 1-Decene with Acidic Ionic Liquid Catalyst

Poly-alpha-olefin (PAO) was researched over acidic ionic liquid catalyzed the oligomerization of 1-decene. Ionic liquid used was 1-butyl-3-methyl imidazolium as a cation and aluminum chloride as an anion, which could effectively catalyze oligomerization and had a higher selectivity. The optimum process conditions for the synthesis of PAO were that the reaction temperature was 160°C, the reaction time was 3 h, the mole ratio between AlCl3 and [Bmim]Cl was 2.5:1, and the count of catalyst was 3 wt%. The components of product were analyzed with gas chromatograph, and the test results showed that the conversion of 1-decene was 74%. The product was the mixture of dimer, trimer, tetramer, and pentamer.

Oligomerization of 1-decene under the action of catalytic systems based on Al-aluminum activator-RCl and Al-RCl

Novel catalytic systems for the cationic oligomerization of 1-decene into synthetic poly(α-olefin) oils have been worked out; these systems include a highly disperse (0.1–40 μm) aluminum, an aluminum activator [I2, Mg, (C2H5)nAlCl3 − n, (CH3)3CCl and some other RX, HCl, benzene, and toluene], and a cocatalyst based on organic halide compounds RX (R is primary, secondary, or tertiary alkyl, allyl, or benzyl; X is Cl, Br, or I). We study the effect of various factors (characteristics of Al, nature of aluminum activator, RCl: Al molar ratio in the catalyst, concentration of Al, temperature, benzene additives, reaction duration) on the conversion of 1-decene into poly(α-olefins), the fractional composition of oligomerization products, the content of chlorine in poly(α-olefins), and the structure and physicochemical characteristics of fractions.

3,5-Dihydroxybenzylalcohol based dendrimers: structure evaluation and molecular encapsulation in generations 1–5

Geometric characterization of 3,5-dihydroxybenzyl alcohol (DHBA)-based dendrimers has been achieved using molecular mechanics MM+ method and the PM3 semi-empirical molecular orbital theory. Optimization of DHBA-based dendrimer generations 1–5 (DG1–5) showed that DG1–3 have a relatively open structure with no internal spaces of any particular size or shape, while DG4 and 5 assume a more globular structure with well-defined internal cavities. Encapsulation of disperse red 1 (DR1) into the cavities of these dimethylsilyl linked DHBA-based dendrimers led to a blue shift in the λmax of DR1, and transmission electron microscopy (TEM) showed a rectangular shape of dendritic aggregates containing DR1. Catalytic activity of (COD)RhCl(PPh2(CH2)3OH) encapsulated in dendritic aggregates below and above critical aggregation concentration (cac) of generations 1–4 was examined. A significant decrease in catalytic conversion of 1-decene to decane in dendrimer generations 4 upon going from a concentration below cac to above cac was observed.

Development of a green process for poly-α-olefin based lubricants

Poly-α-olefin (PAO) based lubricants have a large share of the synlubes market and these are produced in two stages—oligomerisation of α-olefins and hydrogenation. The current industrial processes use AlCl3 and BF3 as catalysts for oligomerisation, which are polluting, hazardous and give a very wide molecular weight distribution. This study reports a green synthesis of a PAO synlube by using 1-decene as the starting material with a variety of solid acidic catalysts, mainly based on clays. The activities for oligomerisation were found to be in the following order: K10 montmorillonite clay > 20% w/w ZnCl2/K10 > 5% w/w (dodecatungstophosphoric acid, DTP)/K10 > 20% DTP/K10 > 10% AlCl3 + 10% FeCl3/K10 > S–ZrO2 > Al-pillared clay > DTP > 20% DTP/carbon. K10 clay gave a conversion of 1-decene of 73% but the selectivities towards the dimer and trimer were 88 and 12%, respectively. 20% ZnCl2/K10 led to a conversion of 68% with 100% dimer formation. The kinetics of reaction were established by using both K-10 and 20% ZnCl2/K10. Oligomerisation is controlled by intrinsic kinetics. The catalysts are reusable. Other olefins such as 1-octene and 1-dodecene were also oligomerized in the presence of 20% ZnCl2/K10. 1-Decene dimer was isolated and then in the next step hydrogenated by employing 20% w/w Ni/SiO2, 20% w/w Ni–Cu (50:50)/SiO2 and a clay anchored bipyridine–montmorillonite–PdCl2 complex as catalysts. Amongst these 20% w/w Ni/SiO2 was found to be the most active catalyst at 50 atm and 150 °C, whereas the anchored catalyst BM–Pd(II) was active at atmospheric pressure and 30 °C. Effects of various parameters were studied to arrive at a kinetic model with both the catalysts. The reactions are intrinsically kinetically controlled showing zero order in dimer concentration and first order in hydrogen partial pressure. 1-Decene based PAO with a viscosity of about 2 cSt has great many applications The hydrogenated product had a viscosity of 2.22 cSt which was found to be comparable with commercially available sample. High-speed spindle oil used in textile industry was also prepared and its performance tested.

Thermoregulated phase transfer ligands and catalysis XIV: Synthesis of N,N-dipolyoxyethylene-substituted-4-(diphenylphosphino) benzenesulfonamide (PEO-DPPSA) and the catalytic activity of its rhodium complex in hydroformylation of 1-decene

A novel water soluble phosphine, N,N-dipolyoxyethylene-substituted-4-(diphenylphosphino) benzenesulfonamide (PEO-DPPSA), is synthesized by ethoxylation of 4-(diphenylphosphino) benzenesulfonamide Ph 2P–C 6H 4SO 2NH 2 (DPPSA) obtained from palladium-catalyzed P–C coupling reaction between 4-I–C 6H 4SO 2NH 2 and Ph 2PH. The PEO-DPPSA possesses the same property of inverse temperature-dependent solubility in water (cloud point, C p) as nonionic surfactants. Investigation on the behavior of RhCl 3·3H 2O/PEO-DPPSA complex in the aqueous–organic biphasic hydroformylation of 1-decene showed that the complex exhibited high catalytic activity. The conversion of 1-decene and the yield of aldehydes reach as high as 97.8 and 95.6%, respectively, under optimized conditions. The high reactivity of Rh/PEO-DPPSA complex can be attributed to a process termed thermoregulated phase transfer catalysis.

Fischer-Tropsch synthesis: carbon-14 tracer study of alkene incorporation

Pentenes, both 1-pentene and a mixture of cis-2- plus trans-2-pentene, are essentially inert toward hydrogenation, incorporation, positional, and perhaps cis-trans isomerization, during Fischer-Tropsch synthesis with a promoted iron catalyst under medium-pressure conditions. 1-Decene does undergo isomerization, hydrogenation, and incorporation, and ethene undergoes the latter two conversions. 1-Decene conversion is believed to be due primarily to hold up in the CSTR. Alkanes appear to be a primary product of the Fischer-Tropsch synthesis and not formed just by secondary reactions